The Most Scandalous Celebrity Love Triangles of All Time

Posted by Susy Alexandre on May 10, 2016, Updated on May 8, 2018

For as long as there have been celebrity love stories, there have been scandalous love triangles that followed. From Liz Taylor to Taylor Swift, it seems few A-listers are immune to a good old-fashioned scandal. Read on for some of the most memorable celebrity love triangles of all time.

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Debbie Reynolds and Eddie Fisher

In the first of what would be three tries at marriage for the American entertainer, Debbie Reynolds took her first walk down the aisle with musician Eddie Fisher in 1955, during which time the couple had two children. It wouldn’t be long before infidelity would rock their marriage and ultimately tear their family apart in what has gone down in history as the most scandalous love triangle of all time…

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Elizabeth Taylor

In the throws of grief after the death of her then-husband Mike Todd, notorious newsmaker Elizabeth Taylor sought comfort in the arms of friend Eddie Fisher. The friendship quickly turned romantic, and the sordid affair is to blame for the end of Fisher’s 5-year marriage to Reynolds. Fresh off his divorce, Fisher would marry Taylor that same year – and their marriage would see the same fate just a few short years later, as Taylor would embark on the love affair of her life with Richard Burton, making her one celebrity who was married two times or more.

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Sandra Bullock and Jesse James

You wouldn’t expect this stunning, talented red carpet staple to have any trouble keeping a man, but it would appear no one is safe from scandal in the Hollywood hills. Sandra Bullock married motorcycle builder and television host Jesse James in 2005 – a mere five years later the couple would divorce, amidst accusations from multiple women who claimed to have had affairs with the troubled James. The divorce made headlines across the globe, going down as one of the messiest celebrity breakups ever, after it was revealed that James’ mistress had been…

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Michelle McGee

Michelle McGee, a 24-year-old former stripper and fetish model, couldn’t stand in starker contrast to the wholesome beauty of Sandra Bullock, and the media frenzy only intensified once McGee took her side of things public. Capitalizing on her 15 minutes of fame, the tattooed model and shamed James did not continue on in their affair after the divorce, with McGee now slamming the former television host and continuing to share details of their once-illicit encounters.

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Brad Pitt and Jennifer Aniston

It took only two years of dating for Hollywood royalty Brad Pitt and Jennifer Aniston to tie the knot. Married in 2000, the two seemed like a perfect match. It came as a surprise to all when, in 2005, Aniston filed for divorce citing “irreconcilable differences.” All would be made clear in due course, however, as tinsel town’s golden boy proved that old habits die hard, even going on to marry his mistress.

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Angelina Jolie

Brad met Angelina Jolie on the set of their spy thriller Mr. and Mrs. Smith. While they both denied relationship rumours at the time, they admitted that this was the time when they fell in love. The now infamous couple went on to adopt three children, have three children (including twins!), and were married in August 2014. Two years later, Angelina would file for divorce citing ‘irreconcilable differences.’ Talk about things coming full circle.

Demi Moore and Ashton Kutcher

When the stunning 41-year-old Demi Moore laid eyes on funnyman Ashton Kutcher in 2003, sparks flew immediately. While Kutcher was 16 years her junior, their surprisingly big age gap didn't matter at first, and it wasn’t long before Kutcher was welcomed into the Moore/Willis clan, even attending family gatherings with Moore and her ex Willis, with whom she remained close. Kutcher seemed to blend seamlessly into the picture, taking on the role of step-dad to Moore’s three daughters, all of whom gave their blessing when the pair married in 2005.

Six years in would find the couple battling rumours of Kutcher’s infidelity, and unlike these celebrity couples who survived cheating and stayed together, in 2011, Moore announced the pair was calling it quits. Though the divorce was only finalized in 2013, Kutcher embarked on his next big relationship early in 2012…

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Mila Kunis

Having spent years playing a couple on television, former That 70’s Show co-star Mila Kunis and Kutcher already had a wealth of history when they reconnected soon after his fallout with Moore. While there’s been plenty of speculation as to the timeline of things, Kutcher and Kunis are still going strong, having given birth to a daughter in 2014 (they're currently expecting their second!) and marrying the following year.

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Reese Witherspoon and Ryan Phillippe

The young lovers – and budding actors – met at Reese’s 21st birthday party and began seeing one other almost immediately, getting engaged the following year and tying the knot in 1999. The pair even acted alongside one another in Cruel Intentions that same year. Seven years later, the marriage would fall apart, with Witherspoon filing for divorce in 2006. Phillippe was slammed in the media amidst rumours of cheating, most notably an alleged affair with…

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Abbie Cornish

Australian actress and musician Abbie Cornish was at the centre of cheating rumours at the time of Phillippe’s divorce from Witherspoon. Considering Phillippe and Cornish carried out a relationship for three years after his split from Witherspoon, it isn’t hard to see why this rumour proved more fact than fiction.

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Taylor Swift and John Mayer

Not so much a love triangle as added fuel to the flame that keeps Taylor Swift’s breakup tracks climbing the charts. It all started with a sweet romance between the pop princess and guitar-toting John Mayer. The notorious ladies’ man is said to have been the catalyst for Swift’s hit “Dear John” – as their brief romance ended not long before the song’s release. John Mayer claims to have been “humiliated” by the track, and one might view it as some sweet revenge that the very same year of his breakup with Swift, the serial dater became involved with one of Swift’s original #girlsquad members…

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Katy Perry

The relationship between Perry and Mayer started a firestorm of feuding between the pop divas, with Swift going as far as to release a track entitled “Bad Blood” that was clearly a direct strike against her former BFF. While Swift maintains her issue with Perry has everything to do with business and nothing to do with boys, we think it’s safe to assume the tryst between her former friend and ex-boyfriend had her seeing RED.

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Meg Ryan and Dennis Quaid

Nineties rom-com screen-queen Meg Ryan married fellow actor Dennis Quaid in 1991, after having gotten together during filming of the movie D.O.A. Rumoured to have married him only on the condition that he resolve his addiction issues, Quaid cleaned up his act and the two made it official. The pair had one child together, before divorcing in 2001 amidst rumours of a longtime affair between Ryan and this notorious industry bad-boy…

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Russel Crowe

It’s alleged that Meg Ryan began her affair with Crowe in 2000, as the two were on set of the film Proof of Life. While Ryan maintains her marriage was finished prior to her involvement with Crowe, she has always maintained that it was her inability to balance work and relationships that destroyed her marriage, not Crowe – who was then labeled as a “home wrecker.”

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Tiger Woods and Elin Nordegren

Former Swedish model-turned nanny for pro golfer Jasper Parnevik met Tiger Woods on the green in 2001, and it wasn’t long before the two made it official in 2004 and had two children together throughout the course of their short-lived marriage. While things officially went south in 2009, when Elin allegedly chased Woods out of their home with a golf club upon confirming a suspected mistress of his, it would later come to surface that Woods had been unfaithful from the very start. It would be his affair with NY nightclub manager Rachel Uchitel that would light the fuse for Nordegren, who confirmed things via texts and voicemails discovered on Woods’ phone, but this, as it turned out, was just the tip of the iceberg…

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How much time do you have?

Nordegren divorced Woods in 2010, despite Woods’ alleged efforts to rehabilitate what he believed was a sex addiction, as allegations from strippers, escorts, waitresses and other countless women continued to pour in, all claiming to have carried out sexual relationships with the shamed golfer. At last count, Woods’ had attested to sleeping with 120 women, one such encounter taking place at his bachelor party prior to his wedding with Nordegren. The scandal rocked not only his personal life, but laid waste to his professional career, getting him booted from countless endorsement deals as his golf game suffered tremendously. Nordegren went on to get her degree in psychology in 2014, as she began dating billionaire Chris Cline, and began to rebuild her life post-Woods’ scandal.

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Dita Von Teese and Marilyn Manson

The gothic musician Marilyn Manson married burlesque entertainer Dita Von Teese in 2005. The pair originally met when Manson asked Teese to be a dancer in one his music videos. The cameo never worked out, but the two continued their friendship and in 2001, soon after Manson and fiancée Rose McGowan ended their engagement, he began seeing Teese. In 2006, just one year after getting hitched, Teese filed for divorce as speculators put the blame on his alleged affair with this young actress…

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Evan Rachel Wood

Evan Rachel Wood was 19 when her and Manson allegedly began their affair – a relationship that ex-wife Teese would allude to in later interviews as the cause for their separation, citing infidelity and alcohol abuse as catalysts for their downfall. Wood and Manson would call it quits in 2010, and in later interviews Manson would unkindly refer to his time with the young actress as “a mistake.”

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Kristen Stewart and Robert Pattinson

Actors Kristen Stewart and Robert Pattinson hooked up in 2008 during filming in a pairing that thrilled Twilight diehards across the world. The sullen-vampire-heartthrob and seemingly sullen real-life actress seemed destined for moody bliss, until leaked photos proved otherwise.

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Rupert Sanders

Kristen Stewart worked with director Rupert Sanders in 2012 on the set of Snow White and the Huntsman, where she’d been cast in one of the leading roles. The tabloids slammed the two when photos were released of the young actress and Huntsman director together – resulting in not one, but two subsequent breakups. Not only did the Twilight lovebirds call it quits, but married father of two Sanders was promptly served divorce papers by his then-wife, model Liberty Ross the following year.